The Evolution of Legal Tech: A 30-Year Perspective with Bob Ambrogi

[00:00:49] Chapter 1: Introductions

Jack Newton: Bob, it’s great to have you here. Thanks for joining me.

I’m thrilled to be in your backyard here in Rockport. You’ve been here for 30 years now—tell me what brought you here.

Bob Ambrogi: I’ve come to this town since I was a kid; my mother loved it here. Eventually, my wife and I decided to check it out, and we’ve been here ever since.

Jack Newton: You’ve been a journalist for nearly 40 years and running your own blog for almost 25. What got you into journalism in the first place?

Bob Ambrogi: This is officially my 30th year as a legal tech journalist. I was a journalist before law school and actually went to law school to advance my journalism career. There are a lot of similarities: gathering facts, finding the truth, and telling a story. After practicing law in the Virgin Islands for a while, I made my way back to legal journalism in Boston and New York.

[00:07:04] Chapter 2: The early days of the web 

Bob Ambrogi: In the early 90s, I became fascinated with the web. In 1995, I published my first piece because I saw the potential for the web to impact law practice. My first column predicted lawyers would use the web for marketing, networking, research, and getting clients.

Jack Newton: You were very prescient. You started the LawSites blog over 22 years ago—a decade before I started Clio.

Bob Ambrogi: The catalyst was a book I wrote about the web for lawyers. As soon as I finished the second edition, it was out of date. I realized books don’t work in a fast-changing environment, so I started the blog to keep people up to date. Back then, the news was so slow I’d scramble for topics; someone putting up a new website was big news.

[00:08:32] Chapter 3: The overlapping circles of law and tech 

Bob Ambrogi: I think of it as a Venn diagram of tech and law practice. When I started, they were hardly even concentric circles; you didn’t need to know anything about tech to practice law. Lawyers still hand-wrote motions and used Martindale-Hubbell books to find referrals. Gradually, those circles overlapped until today, where there is no more periphery. You cannot be a successful lawyer today without fully embracing technology.

Jack Newton: What drove that overlap? Was it the value of the technology or a shift in lawyer mindset?

Bob Ambrogi: It was a changing world. The mobile device was one of the most freeing moments for lawyers, untethering them from their desks. But specifically for law, the advent of the cloud was significant. Clio’s launch was a pivotal moment because it began the movement of practice management to the cloud. Before that, software was clumsy, expensive, and on-premises.

[00:14:17] Chapter 4: The pivotal moment in law

Bob Ambrogi: The pandemic was a pivotal moment where, literally overnight, reluctant lawyers had no choice but to use current tech tools. We were still having programs in 2019 about why lawyers should move to the cloud; by 2020, that conversation wasn’t necessary anymore.

Jack Newton: Have lawyers become more ready to disrupt traditional ways of doing things?

Bob Ambrogi: Lawyers have become savvier consumers. They now demand more from technology—focusing on workflow, integration, and automation. Interestingly, while people focus on “Big Law,” the drive for tech adoption really came from the solo and small firm market early on as a way to level the playing field.

[00:18:14] Chapter 5: The AI wave 

Jack Newton: You’ve seen desktop, cloud, and mobile. Now we have AI. What are the profound impacts you’re seeing?

Bob Ambrogi: AI is already starting to be transformative. Generative AI is based on language—making sense of it and using words to create content—which is exactly what lawyers do. It’s opening up areas like personal injury and litigation, with new tools for the deposition process and drafting documents. In e-discovery, it’s providing new ways to look for “smoking guns” in evidence.

[00:23:29] Chapter 6: The role of the journalist 

Bob Ambrogi: I see my role as a messenger and a consumer advocate. I try to hold vendors to what they say and expose them when things aren’t true. I once exposed a legal tech CEO as a fraud and a thief; he’s now in prison.

Bob Ambrogi: I don’t actually have a tech background. I was a practicing lawyer who thought this stuff was interesting. One advantage I have is that I have to translate tech into terms I understand, which makes it understandable for my audience too.

Jack Newton: It’s harder to stand out now. What’s your advice to a founder today?

Bob Ambrogi: Number one: have a good product that solves a real problem. It’s surprising how many people have a clever idea but never think about whether there is an audience for it. Also, be approachable. Go to shows and trade shows. Use LinkedIn for thought leadership. The legal tech community is still relatively small and warm.

[00:33:18] Chapter 7: Private equity and roll-ups 

Jack Newton: You recently wrote about the amount of private equity coming into legal tech. Is this a good or bad thing?

Bob Ambrogi: In the last decade, most major practice management products have been rolled up into about six major ownership groups. The “good” is that these roll-ups have more capital for development and support. The “bad” is the fear of less competition, which could lead to less innovation and higher prices. Lawyers need to understand who owns their technology and the long-term viability of that business.

[00:40:57] Chapter 8: The cult of innovation 

Jack Newton: ClioCon is coming to Boston this October. You’ve attended every single one.

Bob Ambrogi: I once called it a “cult of innovation”. It’s unlike other conferences because people go there excited about changing the delivery of legal services, not just buying tools.

Bob Ambrogi: A little known fact for you: Boston is where the billable hour was born. A Harvard grad named Reginald Heber Smith developed it for the Boston Legal Aid Society to bring business structure to the organization. He later brought it to the firm Hale and Dorr, and the rest is history.

[00:45:52] Chapter 9: Looking ahead ten years 

Jack Newton: What does the face of legal tech look like in ten years?

Bob Ambrogi: AI will be embedded in every aspect of law practice, as inconspicuous as the cloud is now. Routine tasks will be automated, giving lawyers more time to focus on strategy. I also think we will see a lot less of the billable hour. It doesn’t make sense in the age of generative AI. AI won’t reduce the number of lawyers because the need for legal help is only growing. We have an access to justice crisis where 80% to 90% of people with legal problems aren’t getting help. AI will make it possible to serve those people in different ways.

[00:48:41] Chapter 10: Opportunities for founders 

Jack Newton: What are the highest opportunity areas right now?

Bob Ambrogi: Justice tech. There hasn’t been enough investment there, but there is a huge opportunity to do good and make money while doing it. Also, litigation and personal injury software is ripe for development. The biggest challenge for companies is simply getting noticed amid all the din. You need a unique product that addresses a real need. I see a lot of “copycat” products that don’t distinguish themselves.

Jack Newton: Bob, this has been a fantastic conversation. Thank you for everything you’ve done to shine a spotlight on this space.

Bob Ambrogi: It’s been a great pleasure. Thank you.